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Synthesis of the first alpha-fluoro-phosphotyrosyl mimetic

  1. Author:
    Shi, Z. D.
    Liu, H. P.
    Zhang, M. C.
    Yang, D. J.
    Burke, T. R.

  2. Author Address

    NCI, Ctr Canc Res, Lab Med Chem, NIH, Frederick, MD 20702 USA. Univ Michigan, Sch Med, Dept Hematol Oncol, Ann Arbor, MI USA Burke, TR, NCI, Ctr Canc Res, Lab Med Chem, NIH, POB B Bldg 376 Boyles St, Frederick, MD 20702 USA
    1. Year: 2004
  2. Journal: Synthetic Communications
    1. 34
    2. 21
    3. Pages: 3883-3889
  4. Type of Article: Article
  1. Abstract:

    The diastereoselective preparation of (2S)-2-fluoro-4-1[bis(l, l-dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as. new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)-(+)-4-phenyl-2-oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction-directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included

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External Sources

  1. View record in Web of Science®
  2. WOS: 000224943100006

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